{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:45:47Z","timestamp":1760298347447,"version":"build-2065373602"},"reference-count":104,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2011,4,4]],"date-time":"2011-04-04T00:00:00Z","timestamp":1301875200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Steroid and terpene chemistry still have a great impact on medicinal chemistry. Therefore, the development of new reactions or \u201cgreener\u201d processes in this field is a contemporaneous issue. In this review, the use of bismuth(III) salts, as \u201cecofriendly\u201d reagents\/catalysts, on new chemical processes involving steroids and terpenes as substrates will be focused. Special attention will be given to some mechanistic considerations concerning selected reactions.<\/jats:p>","DOI":"10.3390\/molecules16042884","type":"journal-article","created":{"date-parts":[[2011,4,4]],"date-time":"2011-04-04T10:07:21Z","timestamp":1301911641000},"page":"2884-2913","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Bismuth(III) Reagents in Steroid and Terpene Chemistry"],"prefix":"10.3390","volume":"16","author":[{"given":"Jorge A. R.","family":"Salvador","sequence":"first","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Farmac\u00eautica, Faculdade de Farm\u00e1cia da Universidade de Coimbra, P\u00f3lo das Ci\u00eancias da Sa\u00fade, Azinhaga de Santa Comba, 3000-548, Coimbra, Portugal"}]},{"given":"Samuel M.","family":"Silvestre","sequence":"additional","affiliation":[{"name":"Health Sciences Research Centre, Faculdade de Ci\u00eancias da Sa\u00fade, Universidade da Beira Interior, Av. Infante D. Henrique, 6201-506 Covilh\u00e3, Portugal"}]},{"given":"Rui M. A.","family":"Pinto","sequence":"additional","affiliation":[{"name":"Laborat\u00f3rio de Qu\u00edmica Farmac\u00eautica, Faculdade de Farm\u00e1cia da Universidade de Coimbra, P\u00f3lo das Ci\u00eancias da Sa\u00fade, Azinhaga de Santa Comba, 3000-548, Coimbra, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2011,4,4]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"887","DOI":"10.1039\/c001262a","article-title":"Steroids: Partial synthesis in medicinal chemistry","volume":"27","author":"Hanson","year":"2010","journal-title":"Nat. Prod. Rep."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"408","DOI":"10.1038\/nchembio.2007.5","article-title":"The function of terpene natural product in the natural world","volume":"3","author":"Gershenzon","year":"2007","journal-title":"Nat. Chem. Biol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"259","DOI":"10.1002\/anie.199502591","article-title":"Atom economy - A challenge for organic synthesis: Homogeneous catalysis leads the way","volume":"34","author":"Trost","year":"1995","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1351\/pac200173010103","article-title":"Catalysis for green chemistry","volume":"73","author":"Clark","year":"2001","journal-title":"Pure Appl. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"686","DOI":"10.1021\/ar010065m","article-title":"Origins, current status, and future challenges of green chemistry","volume":"35","author":"Anastas","year":"2002","journal-title":"Acc. Chem. Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2169","DOI":"10.1021\/cr078380v","article-title":"Innovations and green chemistry","volume":"107","author":"Horvath","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Sheldon, R.A. (2008). E factors, green chemistry and catalysis: An odyssey. Chem. Commun., 3352\u20133365.","DOI":"10.1039\/b803584a"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1016\/0010-8545(96)90179-4","article-title":"Bismuth derivatives for the oxidation of organic compounds","volume":"155","author":"Postel","year":"1996","journal-title":"Coord. Chem. Rev."},{"key":"ref_9","unstructured":"Marshall, J.A. (1997). Organic chemistry of Bi(III) compounds. Chemtracts: Org. Chem., 1064\u20131075."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Suzuki, H., Ikegami, T., and Matano, Y. (1997). Bismuth in organic transformations. Synthesis, 249\u2013267.","DOI":"10.1055\/s-1997-1194"},{"key":"ref_11","unstructured":"Suzuki, H., and Matano, Y. (2001). Organobismuth Chemistry, Elsevier."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Vidal, S. (2001). Bismuth(III) derivatives: New catalysts. Synlett, 1194\u20131195.","DOI":"10.1055\/s-2001-15163"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Le Roux, C., and Dubac, J. (2002). Bismuth(III) chloride and triflate: Novel catalysts for acylation and sulfonylation reactions. Survey and mechanistic aspects. Synlett, 181\u2013200.","DOI":"10.1055\/s-2002-19743"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"8373","DOI":"10.1016\/S0040-4020(02)01000-1","article-title":"Applications of bismuth(III) compounds in organic synthesis","volume":"58","author":"Leonard","year":"2002","journal-title":"Tetrahedron"},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Antoniotti, S. (2003). Bismuth(III) tris(trifluoromethanesulfonate). Synlett, 1566\u20131567.","DOI":"10.1055\/s-2003-40866"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"679","DOI":"10.1016\/j.crci.2004.03.008","article-title":"Recent uses of bismuth derivatives in organic synthesis","volume":"7","author":"Antoniotti","year":"2004","journal-title":"C. R. Chim."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Gaspard-Iloughmane, H., and Le Roux, C. (2004). Bismuth(III) triflate in organic synthesis. Eur. J. Org. Chem., 2517\u20132532.","DOI":"10.1002\/ejoc.200300754"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"173","DOI":"10.2174\/1574087054583049","article-title":"Activation of reactions by Lewis acids derived from Ga, In, Sb and Bi","volume":"1","year":"2005","journal-title":"Advances in Organic Synthesis"},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Mulamoottil, V.A. (2005). Bismuth(III) nitrate pentahydrate\u2014A versatile reagent in organic synthesis. Synlett, 2699\u20132700.","DOI":"10.1055\/s-2005-917080"},{"key":"ref_20","first-page":"65","article-title":"Recent advances in the use of bismuth(III) triflate in organic synthesis: an update","volume":"11","year":"2006","journal-title":"Trends Org. Chem."},{"key":"ref_21","unstructured":"Yamamoto, H., and Ishihara, K. (2008). Acid Catalysis for Modern Organic Synthesis, Wiley."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1","DOI":"10.2174\/157017908783497518","article-title":"Recent advances in bismuth-catalyzed organic synthesis","volume":"5","author":"Hua","year":"2008","journal-title":"Curr. Org. Synth."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"241","DOI":"10.2174\/157019309789371587","article-title":"Recent Advances of Bismuth(III) Salts in Organic Chemistry: Application to the Synthesis of Aliphatics, Alicyclics, Aromatics, Amino Acids and Peptides, Terpenes and Steroids of Pharmaceutical Interest","volume":"6","author":"Salvador","year":"2009","journal-title":"Mini-Rev. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"426","DOI":"10.2174\/157017909789108701","article-title":"Recent Advances of Bismuth(III) Salts in Organic Chemistry: Application to the Synthesis of Heterocycles of Pharmaceutical Interest","volume":"6","author":"Salvador","year":"2009","journal-title":"Curr. Org. Synth."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1924","DOI":"10.1002\/anie.200460394","article-title":"\"Designer acids\": Combined acid catalysis for asymmetric synthesis","volume":"44","author":"Yamamoto","year":"2005","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Holden, B., and Rigby, W. (1951). The bismuth-catalysed air-oxidation of acyloins. J. Chem. Soc., 1924\u20131925.","DOI":"10.1039\/jr9510001924"},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Rigby, W. (1951). A new reagent for the oxidation of acyloins to diketones. J. Chem. Soc., 793\u2013795.","DOI":"10.1039\/jr9510000793"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"5513","DOI":"10.1021\/ja01155a578","article-title":"Steroidal sapogenins. 15. Experiments in the hecogenin series (Part 3). Conversion to cortisone","volume":"73","author":"Djerassi","year":"1951","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5533","DOI":"10.1021\/ja01650a077","article-title":"Steroidal sapogenins. 37. Experiments in the hecogenin series (Part 6). Conversion to cortisone","volume":"76","author":"Djerassi","year":"1954","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","unstructured":"Becker, E.J., and Cohen, A. (1965). 12-Keto progestational steroids and derivatives thereof. (3,185,713), US Patent."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"3626","DOI":"10.1021\/jo01286a073","article-title":"Structure and stereochemistry of benzilic acid rearrangement product of 3\u03b1,17\u03b2-diacetoxy-11-Hydroxy-5\u03b2-androst-9(11)-en-12-one","volume":"32","author":"Kurath","year":"1967","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1687","DOI":"10.1021\/ja01540a045","article-title":"2-Hydroxy-\u03941,4-3-keto steroids","volume":"80","author":"Baran","year":"1958","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","unstructured":"Chaudhry, G.R., Halsall, T.G., and Jones, E.R.H. (1961). Chemistry of triterpenes and related compounds. 39. Some derivatives of 4,4-dimethylcholestan-3-one. J. Chem. Soc., 2725\u20132732.","DOI":"10.1039\/jr9610002725"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"788","DOI":"10.1021\/jm00383a017","article-title":"Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives","volume":"28","author":"Marsh","year":"1985","journal-title":"J. Med. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1531","DOI":"10.1021\/jo01041a022","article-title":"A stereospecific synthesis of C-21-methylated corticosteroids","volume":"28","author":"Agnello","year":"1963","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1021\/ja01608a041","article-title":"Schoenocaulon alkaloids. III. The bismuth oxide oxidation of veracevine, cevagenine and cevine","volume":"77","author":"Kupchan","year":"1955","journal-title":"J. Am. Chem. Soc."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"4465","DOI":"10.1021\/ja01573a059","article-title":"The Synthesis of Racemic Piperitenone Oxide and Diosphenolene","volume":"79","author":"Reitsema","year":"1957","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1021\/ja00525a055","article-title":"Total synthesis of (+\/-)-aphidicolin","volume":"102","author":"Corey","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref_39","unstructured":"Lavie, D., and Shvo, Y. (1959). Constituents od Ecballium elaterium L.: Proposed structures for elatericin A and elatericin B. Chem. Ind., 429\u2013430."},{"key":"ref_40","unstructured":"Lavie, D., Shvo, Y., Willner, D., Enslin, P.R., Hugo, J.M., and Norton, K.B. (1959). Interrelationships in the cucurbitacin series. Chem. Ind., 951\u2013952."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"528","DOI":"10.1021\/jo00289a027","article-title":"Synthesis of (+\/-)-15-deoxybruceolide and conversion of (-)-15-deoxybruceolide into (-)-bruceantin: Total synthesis of bruceantin","volume":"55","author":"Sasaki","year":"1990","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"801","DOI":"10.1007\/s11745-004-1299-y","article-title":"Review of chemical synthesis of 7-keto-\u03945-sterols","volume":"39","author":"Parish","year":"2004","journal-title":"Lipids"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2227","DOI":"10.2174\/138527206778742641","article-title":"Catalytic oxidative processes in steroid chemistry: Allylic oxidation, \u03b2-selective epoxidation, alcohol oxidation and remote functionalization reactions","volume":"10","author":"Salvador","year":"2006","journal-title":"Curr. Org. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2581","DOI":"10.1016\/j.tetlet.2005.02.080","article-title":"Bismuth-catalyzed allylic oxidation using t-butyl hydroperoxide","volume":"46","author":"Salvador","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_45","unstructured":"Salvador, J.A.R., and Silvestre, S.M. (2006). Processo para a oxida\u00e7\u00e3o al\u00edlica de compostos insaturados usando hidroper\u00f3xido de t-butilo e catalisadores de bismuto. (103,211), PT Patent."},{"key":"ref_46","unstructured":"Salvador, J.A.R., and Silvestre, S.M. (2006). Faculty of Pharmacy, Unpublished results."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2691","DOI":"10.1081\/SCC-100105397","article-title":"Surface-mediated highly efficient oxidation of alcohols by bismuth nitrate","volume":"31","author":"Samadjar","year":"2001","journal-title":"Synth. Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"764","DOI":"10.1021\/jo00944a031","article-title":"Reactions of bismuth triacetate with organic compounds","volume":"38","author":"Reese","year":"1973","journal-title":"J. Org. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2877","DOI":"10.1002\/1521-3773(20000818)39:16<2877::AID-ANIE2877>3.0.CO;2-V","article-title":"Highly efficient and versatile acylation of alcohols with Bi(OTf)3 as catalyst","volume":"39","author":"Orita","year":"2000","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"8926","DOI":"10.1021\/jo0107453","article-title":"Highly powerful and practical acylation of alcohols with acid anhydride catalyzed by Bi(OTf)3","volume":"66","author":"Orita","year":"2001","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Carrigan, M.D., Freiberg, D.A., Smith, R.C., Zerth, H.M., and Mohan, R.S. (2001). A simple and practical method for large-scale acetylation of alcohols and diols using bismuth triflate. Synthesis, 2091\u20132094.","DOI":"10.1055\/s-2001-18062"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"5851","DOI":"10.1016\/S0040-4020(01)00521-X","article-title":"Bismuth(III) salts as convenient and efficient catalysts for the selective acetylation and benzoylation of alcohols and phenols","volume":"57","author":"Aliyan","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Mohammadpoor-Baltork, I., Khosropour, A.R., and Aliyan, H. (2001). A convenient and chemoselective acetylation and formylation of alcohols and phenols using acetic acid and ethyl formate in the presence of Bi(III) salts. J. Chem. Res. (M), 280\u2013282.","DOI":"10.3184\/030823401103169775"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6775","DOI":"10.1016\/j.tetlet.2004.07.044","article-title":"Facile catalyzed acylation of heteroatoms using BiCl3 generated in situ from the procatalyst BiOCl and acetyl chloride","volume":"45","author":"Ghosh","year":"2004","journal-title":"Tetrahedron Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2433","DOI":"10.1081\/SCC-120006016","article-title":"Bi(III) salts as new catalysts for the selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and formates","volume":"32","author":"Khosropour","year":"2002","journal-title":"Synth. Commun."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1007\/s706-002-8249-1","article-title":"Efficient and selective conversion of trimethylsilyl and tetrahydropyranyl ethers to their corresponding acetates and benzoates catalyzed by bismuth(III) salts","volume":"133","author":"Khosropour","year":"2002","journal-title":"Mon. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1039\/B814448F","article-title":"Bismuth triflate-catalyzed Wagner-Meerwein rearrangement in terpenes. Application to the synthesis of the 18\u03b1-oleanane core and A-neo-18\u03b1-oleanene compounds from lupanes","volume":"7","author":"Salvador","year":"2009","journal-title":"Org. Biomol. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","unstructured":"Stephens, J.R., Butler, P.L., Clow, C.H., Oswald, M.C., Smith, R.C., and Mohan, R.S. (2003). Bismuth triflate: An efficient catalyst for the formation and deprotection of tetrahydropyranyl ethers. Eur. J. Org. Chem., 3827\u20133831.","DOI":"10.1002\/ejoc.200300295"},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Khan, A.T., Ghosh, S., and Choudhury, L.H. (2005). A highly efficient synthetic protocol for tetrahydropyranylation\/depyranylation of alcohols and phenols. Eur. J. Org. Chem., 4891\u20134896.","DOI":"10.1002\/ejoc.200500400"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1917","DOI":"10.1016\/S0040-4020(01)00014-X","article-title":"BiBr3-catalyzed benzylation of alcohols. Stereochemistry and mechanistic investigations","volume":"57","author":"Keramane","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"2562","DOI":"10.1016\/j.jorganchem.2009.04.001","article-title":"Mild and efficient silylation of alcohols and phenols with HMDS using Bi(OTf)3 under solvent-free condition","volume":"694","author":"Kadam","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1027","DOI":"10.1021\/jo016180s","article-title":"A simple and efficient chemoselective method for the catalytic deprotection of acetals and ketals using bismuth triflate","volume":"67","author":"Carrigan","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1016\/j.tetlet.2007.11.127","article-title":"Environmentally friendly organic synthesis using bismuth compounds: Bismuth(III) iodide catalyzed deprotection of acetals","volume":"49","author":"Bailey","year":"2008","journal-title":"Tetrahedron Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1633","DOI":"10.1081\/SCC-120004252","article-title":"Efficient deprotection of tetrahydropyranyl ethers by bismuth(III) salts","volume":"32","author":"Kharamesh","year":"2002","journal-title":"Synth. Commun."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1002\/1615-4169(20010226)343:2<169::AID-ADSC169>3.0.CO;2-C","article-title":"A novel, efficient, and selective cleavage of alkyl tert-butyldimethylsilyl ethers using BiCl3\/NaI system","volume":"343","author":"Sabitha","year":"2001","journal-title":"Adv. Synth. Catal."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"4267","DOI":"10.1016\/S0040-4039(97)00875-7","article-title":"Regeneration of carbonyl compounds from oximes under microwave irradiations","volume":"38","author":"Boruah","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Pinto, R.M.A., Salvador, J.A.R., and Le Roux, C. (2006). Ritter reaction mediated by bismuth(III) salts: One-step conversion of epoxides into vic-acylamino-hydroxy compounds. Synlett, 2047\u20132050.","DOI":"10.1055\/s-2006-949608"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"o3321","DOI":"10.1107\/S1600536807029893","article-title":"5\u03b1-Acetamido-6\u03b2-hydroxy-17-oxoandrostan-3\u03b2-yl acetate","volume":"E63","author":"Pinto","year":"2007","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"o2303","DOI":"10.1107\/S160053680803568X","article-title":"6\u03b2-Acetamido-5\u03b1-hydroxycholestan-3\u03b2-yl acetate","volume":"E64","author":"Pinto","year":"2008","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"7685","DOI":"10.1016\/j.tet.2008.06.006","article-title":"The Lewis acidity of bismuth(III) halides: A DFT analysis","volume":"64","author":"Sanderson","year":"2008","journal-title":"Tetrahedron"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"9221","DOI":"10.1016\/j.tet.2007.06.054","article-title":"Bismuth(III) salts mediated regioselective ring opening of epoxides: An easy route to halohydrins and \u03b2-hydroxy nitrates","volume":"63","author":"Pinto","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"o1420","DOI":"10.1107\/S1600536808019478","article-title":"6\u03b2-Chloro-5\u03b1-hydroxy-20-oxopregnan-3\u03b2-yl acetate","volume":"E64","author":"Pinto","year":"2008","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"o1271","DOI":"10.1107\/S1600536809016997","article-title":"16\u03b1,17\u03b1-Epoxy-5\u03b1-hydroxy-6\u03b2-nitrooxy-20-oxopregnan-3\u03b2-yl acetate","volume":"E65","author":"Pinto","year":"2009","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1002\/chem.200305407","article-title":"Evidence that protons can be the active catalysts in Lewis acid mediated hetero-Michael addition reactions","volume":"10","author":"Wabnitz","year":"2004","journal-title":"Chem. Eur. J."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1909","DOI":"10.1016\/S0040-4020(01)00013-8","article-title":"Reactivity of bismuth(III) halides towards alcohols. A tentative to mechanistic investigation","volume":"57","author":"Keramane","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"2773","DOI":"10.1016\/j.tet.2009.01.100","article-title":"Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphathalate) hexahydrate","volume":"65","author":"Carvalho","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1016\/j.tet.2010.01.089","article-title":"Efficient trans-diaxial hydroxylation of \u03945-steroids","volume":"66","author":"Carvalho","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"7632","DOI":"10.1021\/jm1007769","article-title":"Sterols as anticancer agents: Synthesis of Ring-B oxygenated steroids, cytotoxic profile, and comprehensive SAR analysis","volume":"53","author":"Carvalho","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","unstructured":"Swamy, N.R., and Venkateswarlu, Y. (2002). An efficient method for the synthesis of 2,3-unsaturated glycopyranosides catalyzed by bismuth trichloride in Ferrier rearrangement. Synthesis, 598\u2013600.","DOI":"10.1055\/s-2002-23551"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"884","DOI":"10.3390\/10080884","article-title":"Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the Ferrier rearrangement","volume":"10","author":"Babu","year":"2005","journal-title":"Molecules"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"8507","DOI":"10.1016\/j.tetlet.2005.10.013","article-title":"A study of epoxyolefin cyclizations catalyzed by bismuth trifluoromethanesulfonate and other metal triflates","volume":"46","author":"Lacey","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1979","DOI":"10.1039\/b707001b","article-title":"Highly selective synthesis of oxabicycloalkanes by indium tribromide-mediated cyclization reactions of epoxyalkenes","volume":"5","author":"Smith","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"549","DOI":"10.1016\/j.steroids.2008.01.006","article-title":"Bismuth(III) salt-catalyzed Westphalen and \"backbone\" rearrangements of 5\u03b2,6\u03b2-epoxysteroids. Synthesis and structural elucidation of new olefinic 19-nor and 18,19-dinorsteroids","volume":"73","author":"Pinto","year":"2008","journal-title":"Steroids"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"o214","DOI":"10.1107\/S0108270109010233","article-title":"6\u03b2-Hydroxy-5\u03b2-methyl-20-oxo-19-norpregn-9(10)-en-3\u03b2-yl acetate","volume":"C65","author":"Pinto","year":"2009","journal-title":"Acta Crystallogr. Sect. C"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"o279","DOI":"10.1107\/S0108270108009621","article-title":"5\u03b2,6\u03b2-Epoxy-17-oxoandrostan-3\u03b2-yl acetate and 5\u03b2,6\u03b2-epoxy-20-oxopregnan-3\u03b2-yl acetate","volume":"C64","author":"Pinto","year":"2008","journal-title":"Acta Crystallogr. Sect. C"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"6169","DOI":"10.1016\/j.tet.2009.05.043","article-title":"Bismuth(III) triflate-catalyzed rearrangement of 16\u03b1,17\u03b1-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16\u03b1-substituted 17\u03b1-alkyl-17\u03b2-methyl-\u039413-18-norsteroids","volume":"65","author":"into","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_87","first-page":"705","article-title":"Wagner-Meerwein rearrangements","volume":"3","author":"Pattenden","year":"1991","journal-title":"Comprehensive Organic Synthesis"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"o2088","DOI":"10.1107\/S1600536809030311","article-title":"19\u03b2,28-Epoxy-18\u03b1-olean-3\u03b2-ol","volume":"E65","author":"Santos","year":"2009","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"993","DOI":"10.1016\/S0040-4039(01)02307-3","article-title":"A practical, cheap and environmentally friendly preparation of bismuth(III) trifluoromethanesulfonate","volume":"43","author":"Repichet","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref_90","doi-asserted-by":"crossref","unstructured":"Vat\u00e8le, J.-M. (2008). Lewis acid promoted oxidative rearrangement of tertiary allylic alcohols with the PhIO\/TEMPO System. Synlett, 1785\u20131788.","DOI":"10.1055\/s-2008-1078500"},{"key":"ref_91","first-page":"913","article-title":"Lewis acid-catalyzed oxidative rearrangement of tertiary allylic alcohols mediated by TEMPO","volume":"66","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1016\/S0957-4166(02)00213-6","article-title":"Lewis-acid catalysis of the asymmetric Diels-Alder reaction of dimenthyl fumarate and cyclopentadiene","volume":"13","author":"Kiesman","year":"2002","journal-title":"Tetrahedron Asymm."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1016\/0022-328X(96)06229-8","article-title":"BiCl3-catalyzed Mukaiyama-aldol and carbonyl-ene reactions","volume":"521","author":"Peidro","year":"1996","journal-title":"J. Organomet. Chem."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"7747","DOI":"10.1016\/j.tetlet.2005.09.035","article-title":"Environment friendly organic synthesis using bismuth compounds. An efficient method for carbonyl-ene reactions catalyzed by bismuth triflate","volume":"46","author":"Anderson","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"8017","DOI":"10.1016\/S0040-4039(00)01397-6","article-title":"Surface-mediated highly efficient regioselective nitration of aromatic compounds by bismuth nitrate","volume":"41","author":"Samajdar","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"27","DOI":"10.3998\/ark.5550190.0002.804","article-title":"Montmorillonite impregnated with bismuth nitrate: A versatile reagent for the synthesis of nitro compounds of biological significance","volume":"viii","author":"Samajdar","year":"2001","journal-title":"ARKIVOC"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"3945","DOI":"10.1016\/j.tetlet.2007.04.050","article-title":"Novel nitration of estrone by metal nitrates","volume":"48","author":"Bose","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"o2139","DOI":"10.1107\/S160053681002903X","article-title":"3-Oxo-18\u03b1-olean-28,13\u03b2-olide","volume":"E66","author":"Santos","year":"2010","journal-title":"Acta Crystallogr. Sect. E"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"8488","DOI":"10.1021\/jo9018478","article-title":"Bismuth(III) triflate-catalyzed direct conversion of corticosteroids into highly functionalized 17-ketosteroids by cleavage of the C17-dihydroxyacetone side chain","volume":"74","author":"Pinto","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_100","first-page":"127","article-title":"Synthesis and degradation of the pregnane side-chain","volume":"2","author":"Fried","year":"1972","journal-title":"Organic Reactions in Steroid Chemistry"},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/S0039-128X(02)00173-3","article-title":"A straightforward chemical synthesis of 17-ketosteroids by cleavage of the C-17-dihydroxy acetone side chain in corticosteroids","volume":"68","author":"Leggio","year":"2003","journal-title":"Steroids"},{"key":"ref_102","doi-asserted-by":"crossref","unstructured":"Sun, L., Geng, X., Liu, L.H., Jiang, C.G., and Wang, C. (2009). Iodine-promoted cleavage of the C-17-dihydroxyacetone side chain of corticosteroids in aqueous ammonia water. J. Chem. Res. (M), 22\u201323.","DOI":"10.3184\/030823409X393664"},{"key":"ref_103","first-page":"747","article-title":"Anti-inflammatory steroids","volume":"3","author":"Abraham","year":"2003","journal-title":"Burger's Medicinal Chemistry and Drug Discover: Cardiovascular Agents and Endrocrines"},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"898","DOI":"10.1021\/op025577a","article-title":"A review of the use of aqueous hydrofluoric acid in the manufacture of betamethasone","volume":"6","author":"McGhie","year":"2002","journal-title":"Org. Process Res. 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